HCID 18186386, compound → HCID 69524407, compound

HRID 1358052Notes

Reaction equation

HRID 1358052 reaction equation
Br[C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.[CH3:34][N:35]([CH3:55])[C:36]1[CH:41]=[CH:40][C:39]([Sn](CCCC)(CCCC)CCCC)=[CH:38][N:37]=1>>[CH3:34][N:35]([CH3:55])[C:36]1[N:37]=[CH:38][C:39]([C:2]2[CH:3]=[CH:4][C:5]([CH2:6][CH:7]3[C:16]4[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=5)=[CH:14][CH:15]=4)[CH2:10][CH2:9][N:8]3[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:32][CH:33]=2)=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 18186386HCID 18186386, compoundHCID 18186409HCID 18186409, compound

Product 1

HCID 69524407HCID 69524407, compoundYield 90%

Procedure

The title compound was prepared as described in Example 135, using 1-(4-bromobenzyl)-2-(4-fluorophenyl)-6-(phenylmethoxy)-1,2,3,4-tetrahydroisoquinoline (0.60 g, 0.12 mmol) and 2-(dimethylamino)-5-(tributylstannyl)pyridine to provide the title compound (0.581 g, 90% yield): 1H NMR (CDCl3) 8.42 (dd, 1H), 7.68 (dd, 1H), 7.32-7.45 (m, 7H), 7.06 (d, 2H), 6.91 (m, 2H), 6.72-6.80 (m, 5H), 6.58 (d, 1H), 5.04 (s, 2H), 4.77 (t, 1H), 3.62 (m, 1H), 3.48 (m, 1H), 3.19 (dd, 1H), 3.13 (s, 6H), 2.96 (m, 2H), 2.72 (dt, 1H); ES-MS m/z 544 [M+H]+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-a09910098ee44e69af9e2984b4fab4b1
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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